‘As much a sign of the times as Sgt Pepper or Highway 61 Revisited’ ... Ken Dodd.
Photograph: Edwin Sampson/ANL/REX/Shutterstock/Edwin Sampson/ANL/Rex/Shutterstock

From a distance, Ken Dodd’s musical career seems utterly bizarre. You could understand him having a couple of novelty comedy hits along the lines of Tommy Cooper’s Don’t Jump Off the Roof Dad or Charlie Drake’s My Boomerang Won’t Come Back, but Ken Dodd’s records weren’t funny, or at least the ones that sold weren’t. He knocked out a succession of comedy records, but there were far fewer takers for The Nikky Nokky Noo Song and The Diddly Doo Parade than for the love songs he sang, apparently in deadly earnest.

He specialised in two things. The first were sentimental Italian ballads translated into English – he, or whoever picked songs for him, seemed particularly fond of the oeuvre of Liguria-born MOR singer Wilma Goich – and songs about crying: Tears, Tears of Happiness, I Can’t Hold Back the Tears, Tears Won’t Wash Away These Heartaches, Every Little Tear, Dancing With Tears in My Eyes, Let Me Cry on Your Shoulder. No matter that he made for a deeply improbable romantic balladeer, as evidenced by the sleeves of his albums – with his trademark hair slicked back and his goofy face fixed in a pensive, lovelorn expression, Ken Dodd looked, if anything, even more peculiar than usual. His romantic ballads sold, in occasionally mind-boggling quantities. 1965’s Tears was the biggest-selling single of the year, and the third biggest-selling of the decade: only the Beatles’ She Loves You and I Want to Hold Your Hand shifted more copies. He had 14 Top 30 hits in 15 years: as late as 1980, a Ken Dodd best-of compilation could make the Top 10.

Quick guide

Ten of Ken Dodd's best jokes

My agent died at 90. I always think he was 100 and kept 10% for himself.

I do all the exercises every morning in front of the television – up, down, up, down, up, down. Then the other eyelid.

How many men does it take to change a toilet roll? Nobody knows. It’s never been tried.

What a beautiful day for dashing down to Trafalgar Square and chucking a bucket of whitewash over the pigeons and saying ‘There you are, how do you like it?’

I have kleptomania. But when it gets bad, I take something for it.

What a beautiful day for Dame Nellie Melba to drop a choc-ice down her tights and say ‘How’s that for a knickerbocker glory?’

You’ve got to be a comedian to live there. I call it Mirthy-side.

What a lovely day for knocking on a TV policeman’s door and saying: ‘Hello Mrs Savalas. Have you got a licence for your Telly?’

Did any of us, in our wildest dreams, think we’d live long enough to see the end of the DFS sale?

My dad knew I was going to be a comedian. When I was a baby, he said, ‘Is this a joke?’

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It might look like an inexplicable aberration, but Ken Dodd’s musical career was anything but: it was as much a sign of the times as Sgt Pepper or Highway 61 Revisited. He had his first hit in 1960, and was still knocking records out in 1983, but there’s something very telling about the fact that his biggest commercial success came between 1965 and 1967. These were the years in which, fuelled by a changing diet of drugs, pop music changed more dramatically and rapidly than it ever had before, or indeed has since. By their end, it was virtually unrecognisable: The Beatles in 1964, still the same besuited and bowing-in-unison quartet that had played at the Royal Variety Performance, seemed to have almost nothing in common with the Beatles who appeared on TV on Boxing Day 1967 singing I Am the Walrus.

The success of Ken Dodd’s Tears – a song originally recorded in 1929 towering over a Top 40 that also contained I Can’t Get No Satisfaction, Barry McGuire’s protest anthem Eve of Destruction, Bob Dylan’s Like a Rolling Stone and James Brown’s Papa’s Got a Brand New Bag – was the first sign that a significant proportion of the record-buying public longed not for the white heat of drug-fuelled reinvention, but a simpler, cosier pop era. There’s a forgotten period between the arrival of the UK singles chart and the arrival of Elvis when the Top 10 almost entirely comprised songs that sounded like Tears, the raciest thing on offer was Frankie Laine or Johnnie Ray, and no one in Britain except a handful of die-hard aficionados had any idea about the raucous black American rhythm and blues records that already sounded like the future.

The last generation that came of maturity in that period were still in their 20s when pop first started showing the effects of pot and LSD. They might have found something to love about the Beatles of Do You Want to Know a Secret? or Till There Was You, or the unthreatening sound of Herman’s Hermits singing Mrs Brown You’ve Got a Lovely Daughter. What were they supposed to make of Norwegian Wood or the Kinks’ droning See My Friends? It’s easy to scoff at the 60s squares, but ears trained to love Bing Crosby were clearly going to struggle with the sound of Bob Dylan sneering about not following leaders and watching the parking meters.

Ken Dodd during the run of Doddy’s Here! at the London Palladium in 1965. Photograph: ITV/REX/Shutterstock/ITV/Rex/Shutterstock

Tears was eventually knocked off the No 1 spot by the Rolling Stones’ parent-scaring Get Off of My Cloud, which in turn was deposed by the mum-friendly sound of the Seekers’ The Carnival Is Over. This was a scenario that played out over and over again in the ensuing years. Jim Reeves’ Distant Drums was supplanted by the Four Tops’ groundbreaking Reach Out I’ll Be There, the Beach Boys’ Good Vibrations by Tom Jones’ The Green Green Grass of Home and, perhaps most famously, Englebert Humperdinck’s version of the 1949 song Release Me would relegate Penny Lane and Strawberry Fields Forever to No 2.

Ken Dodd: farewell to the tattifilarious marathon man of comedy

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At the risk of sounding pretentious, it was a kind of battle for the meaning of pop, played out at the top of the charts: was pop music supposed to be entertainment or, as critic Paul Williams put it, “a huge new playground to create and communicate and be perverse in”? Was it meant to be showbiz or the voice of a bohemian subculture? Comforting familiarity or the shock of the new? That Ken Dodd was an unwitting foot soldier in pop’s mid-60s generation gap war might be the weirdest aspect of his career.